Bought During the Pandemic and Not Feeling It Anymore?
If the home you rushed into back in 2020–2022 doesn’t fit the life you’re living now, you’re not stuck. Here’s how to figure out your next move.
I’ve been having a certain conversation a lot lately. It usually starts with something like, “We love Hawaiʻi, but honestly? We’re not sure we love this house.”
These are folks who bought between 2020 and 2022, right in the middle of the craziest market most of us have ever seen. They did what they had to do to win a house. Now, a few years later, the dust has settled and the home just doesn’t fit like it used to.
If that sounds like you, take a breath. You didn’t fail, and you’re definitely not stuck. Let’s talk story about how we got here and what your real options look like today.
How We Got Here
The pandemic market rewarded speed over reflection. Low rates and very few listings meant multiple offers on almost everything, and buyers adjusted to survive:
- Rushed decisions. Homes were seen once, sometimes only on video, and offers went in the same day.
- Stretched budgets. Bidding wars pushed a lot of buyers over asking and past the number they’d planned on.
- Waived protections. Inspection and appraisal contingencies were often the first things to go. For the record, that’s something I would never recommend to my clients, in any market. Those contingencies are there to protect you, and giving them up is how a lot of buyers ended up with surprises they couldn’t afford.
- Compromised priorities. The neighborhood, the yard, the commute, or that extra bedroom got traded away just to land something.
- A life that changed. The spare room that was perfect for remote work matters less now that you’re back in the office. The quiet spot far from town feels a lot farther now that the kids have school, practice, and friends across the island.
None of that means you made a bad call. You made the best decision you could with the information and the market you had at the time.
You’re Not the Only One
Buyer’s remorse after the pandemic boom is well documented. In a national survey by home insurer Hippo, more than three-quarters of recent buyers said they had regrets. Sixty-four percent said they would have bought a different home, and 63% wished they had waited longer.
A separate Clever Real Estate survey found the top reasons were feeling like they overspent (30%) and feeling rushed (26%). About half of recent buyers in the Hippo survey also said owning a home cost more and took more upkeep than they expected.
Here’s the thing: a home that feels like a pair of slippers a size too small is a common problem, and it’s a fixable one. The goal isn’t to beat yourself up about the past. It’s to make a clear-eyed plan for the next five to ten years.
The Good News: Oʻahu Held Its Value
If you bought on Oʻahu during the pandemic, there’s a good chance you’ve built real equity. Through the first nine months of 2026, the island’s median single-family price was up 3.1% to $1,180,000, and the condo median was up 2.5% to $515,000. Back in July 2022, near the height of the frenzy, the single-family median was about $1,108,000.
Homes are still moving, too. In my September market update, single-family homes sold in a median of 16 days at 99.4% of their original list price. Condos are a different story, taking a median of 41 days, so where and what you own matters.
The catch: your interest rate. Many pandemic buyers locked in rates around 3%. Average 30-year rates recently climbed back above 7%. That low rate is one of the most valuable things you own, so any plan should account for what you’d give up by trading it in.
Your Four Options, Island Style
Every situation is different, but most of the folks I talk with land on one of these four paths.
| Option | Best fit when… | Watch out for |
|---|---|---|
| Stay & make it yours | The location works and the house just needs to fit your life better | Remodel costs, permit timelines, and over-improving for the neighborhood |
| Keep it & rent it out | You have a low rate and can qualify for your next home | Landlord duties, vacancies, insurance, and taxes on rental income |
| Sell & move on | The location or size is the real problem and no remodel can fix it | Selling costs and a higher rate on your next loan |
| Wait with a plan | You’re not ready yet, but you know a change is coming | Waiting without a timeline and letting the frustration build |
Stay and make it yours
Sometimes the house is fine and it just needs to work for how you live now. A garage conversion, an updated kitchen, a better lanai setup, or an ADU can completely change how a home feels. Get a contractor and your lender in the conversation before you commit to anything.
Keep it and rent it out
With a 3% rate on your current loan, renting the home and buying something that fits better can pencil out. It only works if the rent covers your costs and you’re honestly up for being a landlord, or willing to pay a property manager.
Sell and move on
Oʻahu single-family sellers are still in a strong spot. If the house is truly holding your family back, listing it may be the cleanest path to the right home. We’ll run your net numbers first so there are no surprises.
Wait with a plan
Not ready to move yet? That’s okay. Set a timeline, track your equity, and knock out small repairs now so you’re ready when the time is right.
For military families: if you bought with a VA loan during the pandemic and new PCS orders are on the horizon, keeping the home as a rental is often worth a look. Talk with your VA lender about your remaining entitlement before you decide, since it affects what you can buy at your next duty station.
Questions to Ask Before You Decide
- What exactly isn’t working: the house itself, the neighborhood, the commute, or the size?
- Can a renovation fix it, or is it something no remodel can change?
- How much equity do I have today, and what would I net after selling costs?
- What would my monthly payment be at today’s rates on the home I actually want?
- Would I be comfortable being a landlord if I kept this home as a rental?
- What does my family need over the next five to ten years?
Write your answers down. In my experience, clarity usually shows up somewhere between question two and question four.
Closing Thoughts
Your home should be the place you’re happy to come back to after a morning on the water or a long day at work, not a source of stress. I spent 20 years in the Coast Guard before becoming a REALTOR®, so I know a thing or two about plans that change. Changing course isn’t a failure. It’s just good seamanship.
If you’re feeling stuck in a pandemic purchase, reach out. We can look at what your home is worth today and map out your options together, no pressure and no rush. 🤙🏽
Not Sure Your Home Still Fits?
Let’s grab a coffee and look at your numbers. I’ll walk you through what your home is worth and what each option could look like for your family.
Let’s ConnectDesmond Cura · REALTOR® · REMAX Hawaiʻi West Oʻahu · (808) 679-5276 · desmondcura.com
Sources: Honolulu Star-Advertiser, Oct. 7, 2026 and July 7, 2026; REMAX Hawaiʻi September 2026 Oʻahu Real Estate Market Reports; Hippo and Clever Real Estate surveys as reported by REALTOR® Magazine. This post is general information, not financial, tax, or legal advice. Information deemed reliable but not guaranteed. Also published on the REMAX Hawaiʻi blog.